USPTO Patents Application 09965610

Applicant : Adam S. Cantor et al. Attorney's Docket No.: 19426-002001 / 56032US022

Serial No. : 09/965,610

Filed : September 26, 2001

Page : 2 of 12

Amendments to the Claims :

This listing of claims replaces all prior versions and listings of claims in the application:
Listing of Claims :

1 . (Currently amended) A transdermal drug delivery composition consisting of
comprising

(a) a copolymer comprising

( i ) one or more A. monomers selected from the group consisting of alkyl acrylates
containing 4 to 12 carbon atoms in the alkyl group and alkyl methacrylates containing 4 to 1 2
carbon atoms in the alkyl group; and

(ii) one or more ethylenically unsaturated B monomers copolymerizable with the
A monomer; and

(b) about S°Ai to about 30% by weight fentanyl based on the total weight of the
co nip o s ition;

wherein the composition is sub tat anti al 1 y free of undissolved fentanyf

2. (Original) The composition of claim 1 wherein the A monomer is selected from the
group consisting of isooctyl acrylate, 2-ethylhexyl aery late, butyl acrylate, and cyclohexyl
acrylate.

3. (Original) The composition of claim 1 wherein the A monomer is isooctyl acrylate.

4. (Original) The composition of claim 1 wherein the B monomer is selected from the
group consisting of 2-hydroxy ethyl acrylate, 2-hydroxyethyl methacrylate, glyceryl acrylate,
N,TsT~diethylacryl amide f 2-ethoxyethoxyethyl acrylate, 2-ethoxyethyl acrylate, tetrahydro fur fury 1
acrylate, acrylic acid, acrylamide, vinyl acetate, N- vinyl pyrrolidone and mixtures thereof.

Applicant : Adam S. Cantor et al. Attorney's Docket No.: 19426-002001 / 56032US022

Serial No. : 09/965,610

Filed : September 26, 2001

Page : 3 of 12

5. (Original) The composition of claim 1 wherein the B monomer is 2-hydroxyethyl
acrylate.

6. (Original) The composition of claim 5 wherein the copolymer comprises from about
S^o to about 45% of 2-hydroxyethyl acrylate by weight based, on the total weight of all
monomers in the copolymer.

7. (Original) The composition of claim 1 wherein the copolymer further comprises a
mac r o monomer.

8. (Original) The composition of claim 7 wherein the mac ro monomer is a functionally
terminated polymethylmethacrylate.

9. (Original) The composition of claim 7 wherein the copolymer contains from about 1
to about 6% of macromonomer by weight based on the total weight of all monomers in the
copolymer.

10-15. (Canceled).

1 0. (Original) The composition of claim 1 wherein the concentration of fentanyl in said
transdermal drug delivery composition is from about 12^ to about 2,4°/o by weight.

17. (Original) The composition of claim 7 wherein the copolymer comprises from about
50 to about 94 C K. isooctyl acrylate, about 5°A> to about 40% 2-hydroxyethyl aery late, about 1 °A> to
about 6*Mj macromonomer, and 0%> to about 2.0 0 A> vinyl acetate by weight.

18. (Original) The composition of claim 7 wherein the copolymer comprises from about
52% to about 60% isooctyl acrylate, about 35°A> to about 40% 2-hydroxyethyl acrylate, about 1°A>
to about 4% macromonomer, and Q°A> to about 10°A> vinyl acetate by weight.

Applicant : Adam S. Cantor et al. Attorney's Docket No.: 19426-002001 / 56032US022

Serial No. : 09/965,610

Filed : September 26, 200 1

Page : 4 of 1 2

19-27. (Canceled).

28. (Original) A method of treating in a mammal a condition capable of treatment by
fentanyl comprising trie steps of:

(a) providing a composition according to claim 1 ;

(b) placing the composition on the skin of a mammal; and

(c) allowing the composition to remain on the skin for a time sufficient to establish or
maintain a therapeutically effective blood level of fentanyl in the mammal .

29. (Original) A method of providing analgesia to a mammal comprising the steps of:

(a) providing a composition according to claim 1 ;

(b) placing the composition on the skin of a mammal; and

(c) placing the composition to remain on the skin for a time sufficient to establish or
maintain an analgesically effective blood level of fentanyl in the mammal,

30. (Previously presented) A method of providing sustained analgesia to a mammal
comprising delivering fentanyl to a mammal via a transdermal drug delivery device in an amount
of about 0.5 to about 5.0 mg/day thereby causing the serum concentration of fentanyl in the
mammal to be about 0.2 to about 10 ng/mL for a period of time from about 4 to about 14 days,
wherein the device includes a composition according to claim 1.

3 1. (Original) The method of claim 30 wherein the fentanyl is delivered in an amount of
0.5 to 2,5 mg/day, the serum concentration of fentanyl in the mammal is about 0,3 to about 4
ng/mL, and the period of time is from about 6 to about 8 days,

32-34. (Canceled).

3 5. (Currently amended) A transdermal drug delivery composition con s isting of
comprising:

(a) a copolymer comprising:

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(i) one or more A monomers selected from the group consisting of isooctyl
acrylate, 2-ethylhexyl acrylate, butyl acrylate, and cyclohexyl acrylate; and

(ii) one or more e tli y 1 e n i c a 1 1 y unsaturated B monomers copolymerizable with the
A monomer; wherein the B monomers are selected from the group consisting of 2-hydroxyethyl
acrylate, 2-hydroxyethyl meth aery late, glyceryl acrylate, ]M,N-diethylacrylamide, 2-
ethoxyethoxyethyl acrylate, 2-ethoxyethyl acrylate, tetrahydrofurfuryl acrylate, acrylic acid,
acryl amide, vinyl acetate, 1ST -vinyl pyrrolidone and mixtures thereof; and

(b) about S°/<> to about 30% by weight fentanyl based on the total weight of the
composition ;

wherein the composition is substantially free of undissolved fentanyl.

36, (Currently amended) A transdermal drug delivery composition consisting of
comprising:

(a) a copolymer comprising:

(i) one or more A monomers selected from the group consisting of isooctyl
acrylate, 2-ethylhexyl acrylate, butyl acrylate, and cyclohexyl acrylate; and

(ii) about 5°A> to about 4 5 * Vb of one or more ethyl enically unsaturated B monomers
copolymerizable with the A monomer; wherein the B monomers are selected from the group
consisting of 2-hydroxyethyl acrylate, 2-hydroxyethyl methacrylate, glyceryl acrylate,
diethylacrylamide, 2-ethoxyethoxyethyl acrylate, 2-ethoxyethyl acrylate, tetrahydrofurfuryl
acrylate, acrylic acid, acryl amide, vinyl acetate, TM- vinyl pyrrolidone and mixtures thereof; and

(b) about &°A> to about 30*X> by weight fentanyl based on the total weight of the
composition;

wherein the composition is substantially free of undissolved fentanyl,

37. (Currently amended) A transdermal drug delivery composition consisting of
compri s ing :

(a) a copolymer comprising

(i) one or more A monomers selected from the group consisting of isooctyl
acrylate, 2-ethylhexyl acrylate, butyl acrylate, and cyclohexyl acrylate; and

Applicant : Adam S. Cantor et al. Attorney's Docket No.: 19426-002001 / 56032US022

Serial No. : 09/965,610

Filed : September 26, 2001

Page : 6 of 12

(ii) about 5°/o to about 45°A> of one or more ethyl enically unsaturated B monomers
copolymerizable with the A monomer, wherein at least one B monomer is 2-hydroxyethyl
acrylate; and

(b) about &°A> to about 30% by weight fentanyl based on the total weight of the
composition;

wherein the composition is substantially free of undissolved fentanyl; and wherein the
drug delivery device delivers fentanyl to a mammal via a transdermal drug delivery device in an
amount of about 0.5 to about 5.0 mg/day thereby causing the serum concentration of fentanyl in
the mammal to be about G.2 to about 10 ng/mL for a period of time from about 4 to about 14
days.

38. (Canceled).

39. (Previously presented). The composition of claim 1 wherein the composition further
comprises a delivery enhancing adjuvant.

40. (Previously presented). The composition of claim 39 wherein the delivery enhancing
adjuvant is selected from the group consisting of alkane polyols, fatty acids, fatty acid esters,
fatty alcohols, terpenes, C5-C18 alkyl esters of a carboxylic acid, and mixtures thereof

41. (Previously presented). The composition of claim 39 wherein the delivery enhancing
adjuvant is selected from the group consisting of ethyl oleate, isopropyl myristate, glycerol,
tetraglycol, methyl laurate, N,N-dimethyldodecylamine IST-oxide, Hmonene, terpineol,
tetraethylene glycol, menthol, and mixtures thereof

42. (Previously presented). The composition of claim 39 wherein the concentration of
the delivery enhancing adjuvant is from about 5 a A> to about A-0°A> by weight based on the total
weight of the composition.

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43. (Previously presented). The composition of claim 39 wherein the skin permeation
enhancer is tetraglycol.

44. (Previously presented). The composition of claim 39 wherein the skin permeation
enhancer is methyl laurate.

fentanyl is from about 12% to about 22% by weight, wherein the composition further comprises
about 15% to about 35% by weight of a permeation enhancer selected from the group consisting
of methyl laurate, tetraglycol, and mixtures thereof.

46. (Previously presented). The composition of claim 45 wherein the concentration of
fentanyl is from about 12% to about 17% by weight and the concentration of methyl laurate is
from about 20% to about 3 5% by weight.

47. (Previously presented). The composition of claim 45 wherein the concentration of
fentanyl is from about 15% to about 22% by weight and the concentration of tetraglycol is from
about 15% to about 25% by weight.

48. (Currently amended). A. pressure sensitive adhesive composition for the transdermal
delivery of fentanyl comprising

(a) an acrylate polymer;

(b) about 8% to about 30% by weight fentanyl based on the total weight of the
composition; and

(c) a delivery enhancing adjuvant selected from the group consisting of methyl laurate,
tetraglycol, and mixtures thereof;

wherein the composition is substantially free of undissolved fentanyl.

45. (Previously presented). The composition of claim 17 wherein the concentration of

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49. (Previously presented). The composition of claim 48 wherein the concentration of
delivery enhancing adjuvant is from about 5% to about A-Q^/o by weight based on the total weight
of the composition,

50. (Previously presented). The composition of claim 48 wherein the acrylate polymer
comprises:

(a) one or more A monomers selected from the group consisting of alkyl acrylates
containing 4 to 1 2 carbon atoms in the alkyl group and alkyl methacrylates containing 4 to 1 2
carbon atoms in the alkyl group; and

(b) one or more ethyl enic ally unsaturated B monomers copolymerizable with the A
monomer.

selected from the group consisting of 2-hydroxyethyl acrylate, 2-hydroxyethyl methacrylate,
glyceryl acrylate, N,N-di ethy aery 1 amide, 2-ethoxyethoxyethyl acrylate, 2 - c th o x yc t h y 1 acrylate,
tetrahydrofurfuryl acrylate, N- vinyl pyrrolidone and mixtures thereof

52. (Previously presented). A device for the transdermal delivery of fentanyl comprising
a backing and a composition according to claim 1 * said composition being adhered to one surface
of the backing.

53. (Previously presented). The composition of claim 39 wherein the delivery enhancing
adjuvant is a skin permeation enhancer.

54. (Previously presented). A transdermal drug delivery composition comprising
(a) a copolymer comprising

(i) one or more A monomers selected from the group consisting of isooctyl
acrylate, 2-ethylhexyl acrylate, butyl acrylate, and cyclohexyl acrylate; and

51. (Previously presented). The composition of claim 50 wherein the B monomer is

Applicant : Adam S. Cantor et al. Attorney's Docket No.: 19426-002001 / 56032US022

Serial ]STo. : 09/965,610

Filed : September 26, 2001

Page : 9 of 12

(ii) about 5°A> to about A-5°A> of one or more ethyl en ic ally unsaturated B monomers
copolymer! zable with the A. monomer; wherein at least one B monomer is 2 -hydroxy ethyl
aery late; and

(b) about S a A> to about 30% by weight fentanyl based on the total weight of the
composition; and

(c) a delivery enhancing adjuvant selected from the group consisting of methyl laurate,
tetraglycol, and mixtures thereof;

wherein the composition is substantially free of undissolved fentanyh

55-91 . (Withdrawn).